Synthesis, Inhaltsverzeichnis Synthesis 2024; 56(16): 2521-2528DOI: 10.1055/a-2323-0721 paper BF3·OEt2-Mediated (3+2) Cycloaddition Reactions of Donor-Acceptor Cyclopropanes (DACs) with Cyanamides: Access to Cyclic Amidines Autor*innen Braj Gopal Prasoon Raj Singh Shubham Bhatt Avijit Goswami∗ Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) This article is dedicated to Prof. Dr. Goverdhan Mehta on the occasion of his 81st birthday. Abstract A BF3·OEt2-promoted facile synthesis of cyclic amidines (2-amino-1-pyrrolines) has been developed via the (3+2)-cycloaddition of cyanamides with donor-acceptor cyclopropanes (DACs). In addition to this, the protocol has been successfully extended to construct a dimerized amidine derivative and gram-scale synthesis with great efficiency. Key words Key wordscyclopropanes - (3+2) cycloaddition - Lewis acid catalysis - cyclic amidines - metal-free - 2-amino-1-pyrroline Volltext Referenzen References 1a Guile SD, Alcaraz L, Birkinshaw TN, Bowers KC, Ebden MR, Furber M, Stocks MJ. J. Med. Chem. 2009; 52: 3123 1b Oehlrich D, Prokopcova H, Gijsen HJ. M. Bioorg. Med. Chem. Lett. 2014; 24: 2033 1c Oleksyszyn J, Boduszek B, Kam CM, Powers JC. J. Med. Chem. 1994; 37: 226 1d Stamford A, Strickland C. Curr. Opin. Chem. Biol. 2013; 17: 320 1e Huang Y, Yi W, Sun Q, Yi F. Adv. Synth. Catal. 2018; 360: 3074 1f McCarthy JR, Wright DL, Schuster AJ, Abdallah AH, Shea PJ, Eysters R. J. Med. Chem. 1985; 28: 1721 2a Greenhill JV, Lue P. Amidines and Guanidines in Medicinal Chemistry . In Progress in Medicinal Chemistry, Vol. 30. Ellis GP, Luscombe DK. Elsevier; Amsterdam: 1993: 206-306 2b Ma Y, De S, Chen C. Tetrahedron 2015; 71: 1145 3a Li G, Zhao M, Xie J, Yao Y, Mou L, Zhang X, Guo X, Sun W, Wang Z, Xu J, Xue J, Hu T, Zhang M, Li M, Hong L. Chem. Sci. 2020; 11: 3586 3b Shriner RL, Neumann FW. Chem. Rev. 1944; 35: 351 3c Zhang Z, Huang B, Qiao G, Zhu L, Xiao F, Chen F, Fu B, Zhang Z. Angew. Chem. Int. Ed. 2017; 56: 4320 3d Veeranna KD, Das KK, Baskaran S. Angew. Chem. Int. Ed. 2017; 56: 16197 3e Saluste C, Crumpler S, Furber M, Whitby R. Tetrahedron Lett. 2004; 45: 6995 4 Hu K, Liu R, Zhou X. Org. Lett. 2021; 23: 6946 5 Hou J, Yang G, Chai Z. J. Org. Chem. 2022; 87: 453 6a Reissig H.-U, Zimmer R. Chem. Rev. 2003; 103: 1151 6b Schneider TF, Kaschel J, Werz DB. Angew. Chem. Int. Ed. 2014; 53: 5504 6c Ghosh K, Das S. Org. Biomol. Chem. 2021; 19: 965 6d Singh P, Varshnaya RK, Dey R, Banerjee P. Adv. Synth. Catal. 2020; 362: 1447 6e Mel’nikov MY, Budynina EM, Ivanova OA, Trushkov IV. Mendeleev Commun. 2011; 21: 293 7a Werz DB, Biju AT. Angew. Chem. Int. Ed. 2020; 59: 3385 7b Grover HK, Emmett MR, Kerr MA. Org. Biomol. Chem. 2015; 13: 655 7c Yu M, Pagenkopf BL. Tetrahedron 2005; 61: 321 8a Beal RB, Dombroski MA, Snider BB. J. Org. Chem. 1986; 51: 4391 8b Yadav VK, Sriramurthy V. Angew. Chem. Int. Ed. 2004; 43: 2669 8c Mackay WD, Fistikci M, Carris RM, Johnson JS. Org. Lett. 2014; 16: 1626 9a Kang Y.-B, Sun X.-L, Tang Y. Angew. Chem. Int. Ed. 2007; 46: 3918 9b Xu P.-W, Liu J.-K, Shen L, Cao Z.-Y, Zhao X.-L, Yan J, Zhou J. Nat. Commun. 2017; 8: 1619 9c Johansen MB, Kerr MA. Org. Lett. 2008; 10: 3497 9d Gopal B, Singh PR, Kumar M, Goswami A. J. Org. Chem. 2023; 88: 132 10a Ivanova OA, Budynina EM, Grishin YK, Trushkov IV, Verteletskii PV. Eur. J. Org. Chem. 2008; 2008: 5329 10b Xu H, Hu J.-L, Wang L, Liao S, Tang Y. J. Am. Chem. Soc. 2015; 137: 8006 10c Augustin AU, Merz JL, Jones PG, Mlostoń G, Werz DB. Org. Lett. 2019; 21: 9405 11 Yang L, He J, Wang H, Xu W, Zhang X, Lang M, Wang J, Peng S. ACS Catal. 2023; 13: 5752 12a Yu M, Pagenkopf BL. J. Am. Chem. Soc. 2003; 125: 8122 12b Pagenkopf BL, Vemula N. Eur. J. Org. Chem. 2017; 2017: 2561 12c Tamilarasan VJ, Srinivasan K. J. Org. Chem. 2019; 84: 8782 12d Sathishkannan G, Srinivasan K. Org. Lett. 2011; 13: 6002 12e Singh PR, Kalaramna P, Ali S, Goswami A. Eur. J. Org. Chem. 2021; 2021: 4683 12f Singh PR, Gopal B, Kumar M, Goswami A. Org. Biomol. Chem. 2022; 20: 4933 13a Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1965; 87: 1353 13b Goldberg AF. G, O’Connor NR, Craig RA. II, Stoltz BM. Org. Lett. 2012; 14: 5314 13c Talukdar R, Tiwari DP, Saha A, Ghorai MK. Org. Lett. 2014; 16: 3954 13d Pohlhaus PD, Sanders SD, Parsons AT, Li W, Johnson JS. J. Am. Chem. Soc. 2008; 130: 8642 13e Andreev IA, Ratmanova NK, Augustin AU, Ivanova OA, Levina II, Khrustalev VN, Werz DB, Trushkov IV. Angew. Chem. Int. Ed. 2021; 60: 7927 14a González-Fernández R, Álvarez D, Crochet P, Cadierno V, Menéndez MI, López R. Catal. Sci. Technol. 2020; 10: 4084 14b Ried W, Kümbel B, Tauer M.-L. Liebigs Ann. Chem. 1984; 564 Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window)
